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Details

Stereochemistry ACHIRAL
Molecular Formula C10H12O4
Molecular Weight 196.2003
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CANTHARIDIN

SMILES

C[C@@]12[C@]3([H])CC[C@]([H])([C@@]2(C)C(=O)OC1=O)O3

InChI

InChIKey=DHZBEENLJMYSHQ-XCVPVQRUSA-N
InChI=1S/C10H12O4/c1-9-5-3-4-6(13-5)10(9,2)8(12)14-7(9)11/h5-6H,3-4H2,1-2H3/t5-,6+,9+,10-

HIDE SMILES / InChI

Description
Curator's Comment:: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/mesh/68002193 and http://www.dormer.ca/DormerCos/WartRemovers.aspx

Cantharidin is a toxic compound, isolated from the Spanish fly or blistering beetle (Lytta (Cantharis) vesicatoria) and other insects. It is a potent and specific inhibitor of protein phosphatases 1 (PP1) and 2A (PP2A). Cantharidin is a medication used to remove warts and a viral skin infection called molluscum contagiosum. It is made from the secretions that come from the green blister beetle in combination with salicylic acid. It works by creating a blister just below the wart, which pushes the wart up and away from the underlying tissue, cutting of the blood supply to the wart. As the blister and the wart dry out, they both slough off, leaving fresh, unmarred skin behind. It is also used as an experimental anti-tumor agent. Several studies also show potential novel applications of cantharidin in acquired perforating dermatosis, acute herpes zoster, and leishmaniasis. In 1962, cantharidin lost Food and Drug Administration (FDA) approval owing to the failure of its manufacturers to submit data attesting to cantharidin's efficacy. However, in 1999, the FDA included cantharidin on its “Bulk Substances List” of drugs which although not available as commercial products, were approved for compounding on a customized basis for individual patients.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Medulloblastoma cell growth
5.0 µM [IC50]
77.64 µM [IC50]
4.2 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
CANTHARONE PLUS

Approved Use

CANTHARONE PLUS is indicated for removal of warts, especially plantar and resistant and heavily keratinized warts.
PubMed

PubMed

TitleDatePubMed
Flavonoids as aryl hydrocarbon receptor agonists/antagonists: effects of structure and cell context.
2003 Dec
[Apoptosis induced by cantharidin in human pulmonary carcinoma cells A549 and its molecular mechanisms].
2005 Jun
Effect of cantharidin, cephalotaxine and homoharringtonine on "in vitro" models of hepatitis B virus (HBV) and bovine viral diarrhoea virus (BVDV) replication.
2007 Jun
Effects of low-dose aspirin on acute inflammatory responses in humans.
2009 Aug 1
A HAMP promoter bioassay system for identifying chemical compounds that modulate hepcidin expression.
2015 May
Patents

Sample Use Guides

Applied topically on the skin
Route of Administration: Topical
In Vitro Use Guide
Cantharidin at concentrations higher than 30 uM rapidly inhibited cell proliferation, with the cells killed in 24 h, treatment with Cantharidin at lower concentrations (1, 5, 10, 20, and 30 uM) was not as toxic at 24 h. For the DAOY cells and treatment for 72 h, for Cantharidin the IC50 for cell viability was 5.0 ± 0.4 uM.
Name Type Language
CANTHARIDIN
MART.   MI   VANDF   WHO-DD  
INN   USAN  
Official Name English
CANTHARIDIN [USAN]
Common Name English
CANTHARIDINE
HSDB  
Common Name English
HEXAHYDRO-3A.ALPHA.,7A.ALPHA.-DIMETHYL-4.BETA.,7.BETA.-EPOXYISOBENZOFURAN-1,3-DIONE
Common Name English
CANTHARIDINUM
HPUS  
Common Name English
(1R,5S,6R,9S)-REL-1,5-DIMETHYL-3,10-DIOXATRICYCLO(3.2.1.01,5)DECANE-2,4-DIONE
Systematic Name English
CANTHARIDIN [MART.]
Common Name English
CANTHARIDIN [VANDF]
Common Name English
2,3-DIMETHYL-7-OXABICYCLO(2.2.1)HEPTANE-2,3-DICARBOXYLIC ANHYDRIDE
Systematic Name English
CANTHARIDIN [INN]
Common Name English
CANTHARIDIN [IARC]
Common Name English
CANTARIDINA
Common Name English
CANTHARIDINE [HSDB]
Common Name English
CANTHARIDIN [WHO-DD]
Common Name English
NSC-61805
Code English
CANTHARIDIN [MI]
Common Name English
EXO-1,2-CIS-DIMETHYL-3,6-EPOXYHEXAHYDROPHTHALIC ANHYDRIDE
Common Name English
CANTHARIDINUM [HPUS]
Common Name English
CANTHARIDES CAMPHOR
Common Name English
HEXAHYDRO-3A,7A-DIMETHYL-4,7-EPOXYISOBENZOFURAN-1,3-DIONE
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 359311
Created by admin on Sat Jun 26 14:17:53 UTC 2021 , Edited by admin on Sat Jun 26 14:17:53 UTC 2021
IARC Cantharidin
Code System Code Type Description
HSDB
2181
Created by admin on Sat Jun 26 14:17:53 UTC 2021 , Edited by admin on Sat Jun 26 14:17:53 UTC 2021
PRIMARY
CAS
56-25-7
Created by admin on Sat Jun 26 14:17:53 UTC 2021 , Edited by admin on Sat Jun 26 14:17:53 UTC 2021
PRIMARY
INN
11470
Created by admin on Sat Jun 26 14:17:53 UTC 2021 , Edited by admin on Sat Jun 26 14:17:53 UTC 2021
PRIMARY
PUBCHEM
5944
Created by admin on Sat Jun 26 14:17:53 UTC 2021 , Edited by admin on Sat Jun 26 14:17:53 UTC 2021
PRIMARY
EVMPD
SUB13227MIG
Created by admin on Sat Jun 26 14:17:53 UTC 2021 , Edited by admin on Sat Jun 26 14:17:53 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-263-3
Created by admin on Sat Jun 26 14:17:53 UTC 2021 , Edited by admin on Sat Jun 26 14:17:53 UTC 2021
PRIMARY
FDA UNII
IGL471WQ8P
Created by admin on Sat Jun 26 14:17:53 UTC 2021 , Edited by admin on Sat Jun 26 14:17:53 UTC 2021
PRIMARY
WIKIPEDIA
CANTHARIDIN
Created by admin on Sat Jun 26 14:17:53 UTC 2021 , Edited by admin on Sat Jun 26 14:17:53 UTC 2021
PRIMARY
DRUG BANK
DB12328
Created by admin on Sat Jun 26 14:17:53 UTC 2021 , Edited by admin on Sat Jun 26 14:17:53 UTC 2021
PRIMARY
EPA CompTox
56-25-7
Created by admin on Sat Jun 26 14:17:53 UTC 2021 , Edited by admin on Sat Jun 26 14:17:53 UTC 2021
PRIMARY
MERCK INDEX
M3025
Created by admin on Sat Jun 26 14:17:53 UTC 2021 , Edited by admin on Sat Jun 26 14:17:53 UTC 2021
PRIMARY Merck Index
MESH
D002193
Created by admin on Sat Jun 26 14:17:53 UTC 2021 , Edited by admin on Sat Jun 26 14:17:53 UTC 2021
PRIMARY
NCI_THESAURUS
C177086
Created by admin on Sat Jun 26 14:17:53 UTC 2021 , Edited by admin on Sat Jun 26 14:17:53 UTC 2021
PRIMARY
RXCUI
1984
Created by admin on Sat Jun 26 14:17:53 UTC 2021 , Edited by admin on Sat Jun 26 14:17:53 UTC 2021
PRIMARY RxNorm